65292-99-1

Usage

Uses

Used in Pharmaceutical Industry:
(3-Methoxyphenyl)acetaldehyde is used as a reagent for the synthesis of isoindoline-1,3-diones and 2,3-dihydrophthalazine-1,4-diones, which are novel B-Raf inhibitors. These compounds have potential applications in the development of targeted therapies for cancer treatment, as they can help inhibit the activity of the B-Raf protein, which is often mutated in various types of cancer.
Additionally, (3-Methoxyphenyl)acetaldehyde is used in the preparation of fluorophenyl-containing piperidine carboxamides, which are novel antihypertensive agents. These compounds have the potential to be developed into new drugs for the treatment of hypertension, as they can help regulate blood pressure by targeting specific receptors or pathways involved in blood pressure regulation.

Upstream product

• 32017-77-9 2-(m-methoxyphenyl)oxirane 
• 16546-34-2 ethyl β-(m-methoxy)phenylglycidate 
• 5020-41-7 2-(3-methoxyphenyl)-ethanol 
• 591-31-1 3-methoxy-benzaldehyde 
• 99334-22-2 methyl 3-(3-methoxyphenyl)glycidate 
• 872-36-6 vinylene carbonate 
• 10365-98-7 3-methoxyphenylboronic acid 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 
• 18927-05-4 methyl (3-methoxyphenyl)acetate 
• 138809-94-6 (S)-(+)-2-(3-methoxyphenyl)oxirane 
• 626-20-0 3-methoxystyrene 
• 1798-09-0 m-methoxyphenylacetic acid 
• 105-39-5 chloroacetic acid ethyl ester 
• 68432-82-6 Na-3-(3-methoxy-phenyl)-glycidat 

Downstream Products

• 1166384-88-8 (4E,2R)-1-(3-methoxyphenyl)-4-hepten-2-ol 
• 1248170-19-5 1-(3-methoxyphenyl)pent-4-en-2-ol 
• 1312943-79-5 C₂₀H₂₂O₆ 
• 4373-67-5 3-(3-methoxyphenyl)pyridine 
• 591-31-1 3-methoxy-benzaldehyde 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 
• 71897-08-0 2-(3-methoxyphenyl)quinoxaline 
• 76098-89-0 (1H-benzo[d]imidazol-2-yl)(3-methoxyphenyl)methanone 

Relevant academic research and scientific papers

Discovery of SARS-CoV-2 main protease inhibitors using a synthesis-directed: De novo design model

The SARS-CoV-2 main viral protease (Mpro) is an attractive target for antivirals given its distinctiveness from host proteases, essentiality in the viral life cycle and conservation across coronaviridae. We launched the COVID Moonshot initiative to rapidly develop patent-free antivirals with open science and open data. Here we report the use of machine learning for de novo design, coupled with synthesis route prediction, in our campaign. We discover novel chemical scaffolds active in biochemical and live virus assays, synthesized with model generated routes. This journal is

Synthetic Access to gem-Difluoropropargyl Vinyl Ethers and Their Application to Propargyl Claisen Rearrangement

With the increasing importance of fluorine to medicinal chemistry and other areas, methods to access various fluorinated compounds are needed. Herein, we report the synthesis of difluoropropargyl vinyl ethers from ketones and aldehydes using difluoropropargyl bromide dicobalt complexes. We applied difluoropropargyl vinyl ethers to the synthesis of difluorodienone or difluoroallene under thermal conditions and trifluoro-pyran under acid-catalyzed conditions.

Kinetic Resolution of Neopentylic Secondary Alcohols by Cu-H-Catalyzed Enantioselective Silylation with Hydrosilanes

A nonenzymatic kinetic resolution of sterically congested alcohols having a quaternary carbon atom in the β-position is reported. The catalyst system CuCl/NaOtBu/(R,R)-Ph-BPE together with a 3,5-xylyl-substituted tertiary hydrosilane enable enantioselective silylation of the hydroxy group. Several alcohols are obtained with good to excellent selectivity factors, and there are no other known straightforward methods to access these motifs.

Synthesis of Arylacetaldehydes by Iridium-Catalyzed Arylation of Vinylene Carbonate with Arylboronic Acids

The one-step synthesis of arylacetaldehydes by carbon–carbon bond formation between formylmethyl and aryl groups has been realized by the reaction of vinylene carbonate with arylboronic acids in the presence of an iridium/bisphosphine catalyst and a catalytic amount of tetrahydroxydiboron.

Transaminase-Catalyzed Continuous Synthesis of Biogenic Aldehydes

The physiological role of biogenic aldehydes, such as 3,4-dihydroxyphenylacetaldehyde (DOPAL), has been associated with cardiovascular and neurodegenerative disorders. The availability of these substrates is limited and robust synthetic methodologies would greatly facilitate further biological studies. Herein, a transaminase-mediated single-step process in continuous mode, which leads to excellent product yields (90–95 %), is reported. Coimmobilization of the pyridoxal phosphate (PLP) cofactor eliminated the need for exogenous addition of this reagent without affecting the longevity of the system, delivering a truly self-sufficient process.

Stereoselective Synthesis of Vinylboronates by Rh-Catalyzed Borylation of Stereoisomeric Mixtures

The stereoselective preparation of vinylboronates via rhodium-catalyzed borylation of E/Z mixtures of vinyl actetates is described, and this method was also extended to synthesis of vinyldiboronates. These transformations feature high functional group compatibility and mild reaction conditions. Control experiments support a mechanism that involved a Rh-catalyzed borylation-isomerization sequence. The isomerization of (Z)-vinylboronates to (E)-isomers was also demonstrated.

Novel Hypoxia-Inducible Factor 1α (HIF-1α) Inhibitors for Angiogenesis-Related Ocular Diseases: Discovery of a Novel Scaffold via Ring-Truncation Strategy

Ocular diseases featuring pathologic neovascularization are the leading cause of blindness, and anti-VEGF agents have been conventionally used to treat these diseases. Recently, regulating factors upstream of VEGF, such as HIF-1α, have emerged as a desirable therapeutic approach because the use of anti-VEGF agents is currently being reconsidered due to the VEGF action as a trophic factor. Here, we report a novel scaffold discovered through the complete structure-activity relationship of ring-truncated deguelin analogs in HIF-1α inhibition. Interestingly, analog 6i possessing a 2-fluorobenzene moiety instead of a dimethoxybenzene moiety exhibited excellent HIF-1α inhibitory activity, with an IC50 value of 100 nM. In particular, the further ring-truncated analog 34f, which showed enhanced HIF-1α inhibitory activity compared to analog 2 previously reported by us, inhibited in vitro angiogenesis and effectively suppressed hypoxia-mediated retinal neovascularization. Importantly, the heteroatom-substituted benzene ring as a key structural feature of analog 34f was identified as a novel scaffold for HIF-1α inhibitors that can be used in lieu of a chromene ring.

New Stereoselective Biocatalysts for Carboligation and Retro-Aldol Cleavage Reactions Derived from d-Fructose 6-Phosphate Aldolase

d-Fructose 6-phosphate aldolase (FSA) catalyzes the asymmetric cross-aldol addition of phenylacetaldehyde and hydroxyacetone. We conducted structure-guided saturation mutagenesis of noncatalytic active-site residues to produce new FSA variants, with the goal of widening the substrate scope of the wild-type enzyme toward a range of para- A nd meta-substituted arylated aldehydes. After a single generation of mutagenesis and selection, enzymes with diverse substrate selectivity scopes were identified. The kinetic parameters and stereoselectivities for a subset of enzyme/substrate combinations were determined for the reactions in both the aldol addition and cleavage reaction directions. The achieved collection of new aldolase enzymes provides new tools for controlled asymmetric synthesis of substituted aldols.

Molecular structures of cdc2-like kinases in complex with a new inhibitor chemotype

Cdc2-like kinases (CLKs) represent a family of serine-threonine kinases involved in the regulation of splicing by phosphorylation of SR-proteins and other splicing factors. Although compounds acting against CLKs have been described, only a few show select

Synthesis of Substrates for Aldolase-Catalysed Reactions: A Comparison of Methods for the Synthesis of Substituted Phenylacetaldehydes

Methods for the synthesis of phenylacetaldehydes (oxidation, one-carbon chain extension) were compared by using the synthesis of 4-methoxyphenylacetaldehyde as a model example. Oxidations of 4-methoxyphenylethanol with activated DMSO (Swern oxidation) or manganese dioxide gave unsatisfactory results; whereas oxidation with 2-iodoxybenzoic acid (IBX) produced 4-methoxyphenylacetaldehyde in reasonable (75%) yield. However, Wittig-type one-carbon chain extension with methoxymethylene-triphenylphosphine followed by hydrolysis gave an excellent (81% overall) yield of 4-methoxyphenylacetaldehyde from 4-methoxybenzaldehyde (a cheap starting material). This approach was subsequently used to synthesise a set of 10 substituted phenylacetaldehydes in good to excellent yields.